First Dates & What to Wear
Dating is stressful enough. Your outfit doesn't have to be.
In this Nat Chat, Natalie shares her approach to first date style, why she believes your best date outfit is probably already hanging in your closet, and how a few go-to looks can help you show up as yourself, no matter where the date takes you.
Episode Notes & Resources:
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Read the full & Raw Episode transcript:
[00:00]
Welcome, everyone, to another Wear Who You Are Wednesday, my favorite day of the week. Today's Nat Chat episode. And as you know, I answer questions straight from you like I'm sitting in your living room or in a wardrobe session.
And this question today was one that I was really excited to answer. It came from Devin in New York City. Devin asked, “I'm out in the dating world. What are your recommendations for dressing for a first date?”
[00:40]
I love this question, and I love it for a lot of reasons. One, because I think we put way too much pressure on a first-date outfit, looking outward at the person that you're going on the date with, not thinking about what you feel most yourself and confident in. So all of a sudden, we can picture this scene: all your clothes are on the bed, you've put on like 27 things, nothing feels right. You're sending pictures to your friends, you're wondering if you're overdressed or underdressed, yada yada yada. Should you panic shop for something?
And then you're in this hamster wheel cycle and already working yourself up for this date. I want you to avoid that. I promise there is an easier and there is a more aligned way. And we're going to talk about that. And I'm giving you permission to do this, and I'm asking you: do not panic shop before a date.
[01:35]
Dating already comes with so many unknowns. Even if you've been, I'll call it, dating as pen pals with someone for weeks, that can bring even more pressure to the date. You don't know if you're going to click, and you don't know how the conversation will flow when you're together. You don't know if you need to maybe text your friend and ask her to call if there's an emergency. Like, that's a lot of stuff going into it. And I really don't want your outfit to be another unknown or another cause of stress.
So, Devin and anyone else out there in the dating world, here's what I actually recommend when it comes to your dating style strategy. So let's think about it. If we were working together, if I were in your house with you doing a wardrobe session, this is exactly what we would do.
[02:20]
I would want you to create two or three go-to outfit formulas, ones that you love, not outfits for one specific restaurant or one specific person. I want you to have a complete outfit formula that you feel great in. So how do we do this? I would start by asking you to pull out pieces in your closet that you feel the best in no matter what. Like your freaking hero. I love this piece. This piece excites me. I wear it all the time. I feel amazing in it. Those are the pieces you're gonna pull out first.
And then we would build outfit formulas around those. So maybe yours is a great pair of jeans and an elevated blouse and, like, a leather jacket that you love. Maybe it's an easy-breezy favorite dress that you have a layer and a shoe that you love to go with it. Maybe it's a pair of trousers and a knit top. I really don't care what the formula is. I care most that it feels like you. It's one of your favorite things and you are feeling yourself in it, right?
[03:20]
So then after that, you've got these formulas, these different outfit combinations. Then I want you to think about the different kinds of dates that you could go on. Maybe you go on a lot of coffee dates. Maybe it's drinks after work, maybe it's dinner, a museum, a walk. Think about the seasons that you're in and the time of day too. Okay.
So take those outfit formulas you created, and we're gonna flex them. Swap in a different shoe that's maybe a little bit dressier. Swap in a shoe that's good for a walk or a morning. Change the layer, change the jacket, add a trench, put on different jewelry. Like, find different ways to wear those favorite formulas, those basically, like, core pieces, the Core’drobe pieces of your dating that you have.
[04:10]
So the foundation is really gonna stay the same, like the hero pieces, the ones that you love, but you have different versions of it for different date situations. Again, this is all about you and it's all about the settings.
So then what I really want you to do, and please take the time to do it, is to photograph these outfits. I'm really serious about this because I can't tell you the number of times I've put together outfits for clients, and then they say, “Yeah, yeah, I'll remember that.” And then I get a text 10 minutes later, the next day, two days later: “What did we do with that blazer?”
That's why when I do any sort of wardrobe session or style session with a client, I snap a quick picture, not even professional, just, like, a reference picture so that they know what they have. So give yourself that mental insurance. Take a mirror selfie or just lay the pieces on your bed together, whatever works for you, and then create an album in your phone that says, “Date night outfits,” “Date nights,” whatever you want it to be. But note that these are your specific outfits that you feel amazing in, you've tried them on, and you know the different versions of them that you can put together.
[05:15]
So then when that date comes, whether it's planned in advance or maybe it's a more spontaneous, “Hey, you free for drinks tomorrow?” you're not standing in your closet starting from scratch. You can simply choose version A, B, or C of one of the outfits that you put together.
I want you to be present. I don't want you to be worrying in your head about what you're wearing, not fidgeting with something, wondering, “My gosh, we're walking more than I thought, and these shoes were a mistake. I've never worn them before.” I just—I don't want you to have any of that worry in your head.
I'll be honest, I didn't always do this. Do as I say, not what I did. I definitely went through phases when I was actively dating and I would dress differently depending on the guy.
[06:05]
I thought, “He likes someone who dresses like this,” or, “Maybe I should wear something more...” dot, dot, dot, whatever it was. I was actually, truthfully, letting my own profession get in the way. I knew how to dress to attract a specific person, but I wasn't really dressing for me. It was absolutely exhausting. It had an impact on my closet. It had an impact on the total relationship, honestly, for those that lasted more than, like, two or three dates.
Because I was presenting an edited version of myself from the get-go, and I was dressing for that male's gaze and not his interests. So my own style preferences and explorations weren't in the forefront. So I really, truly wasn't putting forth all of who I was. And so every time I think about that, I'm like, wow, that can really get in the way of our own style discovery and really presenting who we are in a dating scenario from the get-go to cut through, quite frankly, some of the BS.
[07:05]
I think about—I don't know if you have seen the movie Runaway Bride. It's a, I think, a '90s, early 2000 movie. But anyway, in this movie, Julia Roberts is the protagonist, and she famously is a runaway bride, as the movie says. And every person that she's with, she would order their eggs however they ordered them. And so she, you know, if they got scrambled, she got scrambled. If they got over easy, she got over easy, over easy.
And then at one point in the movie, she realizes she doesn't even know what kind of egg she likes because she spent so much time trying to adjust to the person that she's with and the person that she thought the person she was with—like, the version of herself that the person that she was with would like, right?
So that's how I feel about style. When you're totally adjusting to that person, then you start losing your own self and your own way of dressing.
[07:55]
So I say repeat the outfits. Create the formula, have those versions of you that you love, that you do your power pose in, that you feel amazing in, and you feel comfortable, attractive, like yourself, whatever your goals are, because your outfit is doing then exactly what it's supposed to do. It's supporting the conversation, it's showing who you are, and it's not becoming an internal conversation in your head that you're gonna have with yourself worrying about what you're wearing.
Instead, you're putting yourself in a much better way to get to know somebody by being stylistically aligned with who you are.
Thanks so much for that question, Devin. I hope it was helpful for you. I hope it was helpful for anyone else out there in the dating world. Good luck out there. And just remember, you are perfect exactly as you are, and wear that proudly. Have a great day. See you next time.